1H-1,2,4-Triazole → HCID 11395197, compound

HRID 1886873Notes

Reaction equation

HRID 1886873 reaction equation
[NH:1]1C=NC=N1.P(Cl)(Cl)(Cl)=O.[N:11]1([C:19]([CH2:21][C@H:22]([CH2:35][OH:36])[O:23][CH2:24][P:25]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[O:20])[CH:18]=[CH:17][C:15](=O)[NH:14][C:12]1=[O:13]>N1C=CC=CC=1>[N:11]1([C:19]([CH2:21][C@H:22]([CH2:35][OH:36])[O:23][CH2:24][P:25]([O:31][CH:32]([CH3:34])[CH3:33])([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])=[O:20])[CH:18]=[CH:17][C:15]([NH2:1])=[N:14][C:12]1=[O:13]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 11326794HCID 11326794, compound

Product 1

HCID 11395197HCID 11395197, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 1,2,4-triazole (662 mg, 9.6 mmol) in 15 mL pyridine was added phosphorousoxychloride (223 μL, 2.4 mmol) at room temperature. The mixture was stirred for 10 minutes. Then the solution of 21 (289 mg, 0.80 mmol) was added to the mixture. The reaction mixture was stirred for 4 hours. Then ammonia gas was bubbled in to the reaction mixture for 1-3 hours and the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (CH2Cl2:MeOH=12:1) to give compound 22 (220 mg, 0.58 mmol) as a colorless foam, in 73% yield, which was characterized as follows:

Workup

  1. stirringThe reaction mixture was stirred for 4 hours
  2. customThen ammonia gas was bubbled in to the reaction mixture for 1-3 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by column chromatography (CH2Cl2:MeOH=12:1)

Sources & evidence

ORD record
ord-6ba0d6dce10442c1ada59e9997aadd73
Source dataset
uspto-grants-2013_08
Patent number
US08501709B2

Reaction notes

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